Question

A. i) Ho^ OH, TOH, Dean-Stark; ii) Pd/C, H2; iii) EtBr; iv) H2O, HCI B. i) 2 EVOH, TOH, Dean-Stark; ii) a) MeLi, b) EtBr; iii) H2O, HCl; iv) Pd/C, H, C. i) excess EtOH, H2SO4, heat; ii) a) MeMgBr, b) EtBr; iii) Pd/C, Hz; iv) H.O, HCI D. A and C would both work E. B and C would both work

Answer 1

Eto oft Excess Etot 3- Hy sou heat I Meng By oft Eto ott + Et put J pole, Hz

In the first step, the aromatic ketone is protected as ketal with Ethanal in tyhe presence of catalytic amount of H2SO4. In the second step, the terminal alkyne is treated with methyl magnesium bromide followed by the addition of ethyl bromide gives the alkylated product. The internal alkyne on treatment with Pd/C, H2 followed by treatment with H2O, HCl gives the final product.

The correct option : C